Salt of a quinolin carboxylic acid and process of producing the same



Patented Feb. 22, 1927.

UNITED STATES MOSES L. CROSSLEY, 0F SOMERVTLLE, NEXV JERSEY, ASSIGNOR TOTHE CALCO CHEML CAL COMPANY, OF BOUNDBROOK, NEW JERSEY, A CORPORATION OFNEW JERSEY.

SALT OF A QUINOLIN CAEBOXYLIC ACID AND IPIROGESS OF PRODUCING THE SAME.

NoZDrawing.

This invention relates generally to a salt of a quinolin carboxylic acidand the process of preparing same, and more particularly to a metallicsalt ot.an ar'yl quinolin carboxylic acid. as the magnesium salt of suchorganic compound. The particular salt to which this invention hasespecial reference is the magnesium salt of-2-phenylquinolinl-carboxylic acid, or cinchophen. The anhydrous form ofsuch salt has the structural formula:

(la W.

and in the hydrated forms the formulae:

This new product maybe prepared by treating an aryl phenylquinolincarboxylic acid with a magnesium compound in either an aqueous or. analcoholic solution. The method torproducing such new product in which anaqueous medium is used is as follows: a

.50 parts of pure Q-phenylquinolint-carboxylic acid are warmed withamixture oi 10 parts of magnesium oxide and 1000 parts of w'ater and themixture stirred thoroughly for several hours. The supernatant liquor isdecanted off through a filterand the solid residue again treated withhot water and filtered. The lixiviation iseoutinued untilnothing furtheris extracted. The combined liquor is then concentrated to aboutone-fifth of its original volume and allowed to cool. The saltcrystallizes as hydrates containing 4 and 8 molecules of wav ter ofcrystallization. ,lVhcu heated these hydrates lose water and theanhydrous salt results. The first crop of crystals represents about 85percent of the weight of the acid taken. The mother liquor is worked upto recover the salt it containseither as Application filed September 20,1924. Serial N0.738,912.

such or as the acid. The salt is washed tallized out. I

The resulting magnesium salt of 2-phenylquinolin-4-carbox'ylic acid whenanhydrous is yellow in color and has a slightly bitter taste. It formshydrates containing 4 and 8 molecules of water respectively. The

hydrate with 4 molecules of water separates from aqueous solution bestabove 80 C. From a supersaturated solution the hydrate containing 8molecules of water separates best at temperatures below 80 C. Thishydrate melts in hot water at about 68 (3., passing over into thehydrate con taining 4 molecules of water, which then precipitates.

This new organic compound salt is soluble in water and certainorganicsolvents. such as alcohols. for example: methyl alcohol. ethylalcohol, propyl alcohol: acetone. methyl acetate, aniline. andnitrohenzene.

The novel product has pronounced therapeutic properties. and is eflective in the treatment of gout, rheumatic fever and kindred ailments.

Having thus described the invention. what I claim as new and desire tosecure bv-Letters Patentof the United States is: I

1. As a new product. a magnesium salt of 2'-phenylquinolinl-carhoxylicacid.-

2. As anew product. a magnesium salt of 2-phenylquinolinl-carboxylicacid containmg .not less than four molecules of water ofcrystallization.

3. As a new produ'ct,- a magnesium salt of 2-phenylquinolin-4-carhoxylic acid containing not more than eightmolecules of water of crystallization.

4. As a new product. a magnesium salt of Z-phenylquiuolinl-carboxylicacid containing not less than four and not more than eight molecules ofwater of crystallization.

In testimony whereof I have signed the foregoing specification. MOSES L.CROSSLEY.

